Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

5.3K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
5.3K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

3.0K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.0K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

5.6K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
5.6K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.0K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
8.0K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

5.6K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the...
5.6K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.2K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.2K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Construction of a thiourea-functionalized metallomacrocycle for the reductive amination of furfural under mild conditions.

Dalton transactions (Cambridge, England : 2003)·2026
Same author

Efficient Light-Driven CO<sub>2</sub> Capture and Reversible Release Enabled by Metastable Photoacid-Decorated Metal-Organic Frameworks.

Journal of the American Chemical Society·2026
Same author

Photoinduced Alkene Carbothiolation via Fe/Ni Dual Catalysis.

Organic letters·2026
Same author

A dye-loaded Fe<sub>4</sub>L<sub>4</sub> cage for efficient photocatalytic C(sp<sup>3</sup>)-H activation.

Dalton transactions (Cambridge, England : 2003)·2026
Same author

Reactivity of a d<sup>2</sup> Mo(IV) Alkylidyne Fragment Bearing a PNCNP Pincer Ligand Toward Alkynes: Coordination and Catalytic Alkyne Metathesis.

Angewandte Chemie (International ed. in English)·2026
Same author

Merging bioinspired incubation with supramolecular photocatalysis for Michaelis CO<sub>2</sub> reduction beyond enzymes.

Nature communications·2026

Related Experiment Video

Updated: May 7, 2025

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron

Published on: August 12, 2019

7.9K

Selective Arene Photonitration via Iron-Complex β-Homolysis.

Shuyang Liu1, Ziyu Gan1, Min Jiang2

  • 1State Key Laboratory of Fine Chemicals, School of Chemistry, Dalian University of Technology, Dalian 116024, China.

JACS Au
|December 30, 2024
PubMed
Summary

This study introduces a novel visible-light-driven method for arene C-H nitration, offering an efficient and eco-friendly alternative to traditional nitration processes. The new strategy utilizes a biocompatible system and a unique nitryl radical mechanism for improved results.

More Related Videos

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.1K
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

9.1K

Related Experiment Videos

Last Updated: May 7, 2025

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron

Published on: August 12, 2019

7.9K
The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.1K
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

9.1K

Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Photochemistry

Background:

  • Nitroaromatics are vital compounds in pharmaceuticals, dyes, and materials, but their synthesis via traditional nitration is environmentally problematic.
  • Current nitration methods suffer from pollution, poor selectivity, and difficult purification, necessitating greener alternatives.

Purpose of the Study:

  • To develop a mild, efficient, and environmentally friendly visible-light-driven strategy for arene C-H nitration.
  • To overcome the limitations of conventional nitration techniques, enhancing substrate applicability and functional group tolerance.

Main Methods:

  • Development of a visible-light-driven photocatalytic system using a biocompatible ferric-nitrate complex.
  • Investigation of the reaction mechanism involving β-homolysis of the photoexcited complex to generate a nitryl radical.
  • Demonstration of the strategy's effectiveness in various synthetic applications, including scale-up and late-stage functionalization.

Main Results:

  • Achieved efficient and regioselective arene C-H nitration under mild, visible-light conditions.
  • Exhibited excellent substrate applicability and functional group tolerance, outperforming traditional methods.
  • Successfully applied the strategy in scale-up synthesis, total synthesis, and late-stage functionalization of complex molecules.

Conclusions:

  • The proposed visible-light-driven nitration strategy offers a sustainable and effective approach to synthesizing nitroaromatics.
  • The novel nitryl radical generation mechanism provides new insights into C-H functionalization.
  • This method holds significant potential for greener industrial applications and advanced organic synthesis.